Starting a new business is tough even for those who grow up with entrepreneurial parents and assume they, too, will one day become their own bosses. Part of the challenge lies in the fact that most entrepreneurs prefer to forget the traumatic early days. They're not likely to bring up the maxed-out credit cards, sleepless nights, and calls and letters from creditors in polite conversation.

Those interviewed for this article all faced another hurdle: They were not just starting traditional brokerage firms, but were determined to launch broker-as-advisor businesses offering innovative products and services. And while that's a noble undertaking, making a living selling the unfamiliar to a market used to the traditional is a tough row to hoe.

There's a huge difference between being self-employed and being an entrepreneur, says Allison De Paoli, founder and CEO at De Paoli Professional Services LLC. “If you just want to be your own boss, you can start another brokerage firm selling traditional products,” she says. “Before going out on your own, I would think hard about whether you want to be self-employed or an entrepreneur. I wanted to be an entrepreneur, which meant I had to create everything from scratch.”

There's no single playbook for success, but from each of these advisors' experiences—Adam Berkowitz; Allison De Paoli; Kareim Cade (founder and president of Great Lakes Benefits Group); Megan Cook (Adept Benefits); and Niko Caparisos (Prosperity Benefits)—nuggets of very hard-won wisdom emerge.

Preflight

At what point in one's career does being the ultimate boss begin to seem like a good idea? Berkowitz had certainly thought about how he would run the show if he were in charge. He got his start in health insurance with a local firm during the recession. Like many young brokers new to the business, he gravitated toward consulting with clients on meeting the requirements of the Affordable Care Act.

“I carved out a niche within the firm. I was definitely intrapreneurial,” he says. He was also unencumbered by a background in traditional health insurance products. “All I knew was constant motion.” So when the hammer came down on his son's birth day, he was ready to become a benefits innovator.

De Paoli, meanwhile, was brought up in an extended family of serial entrepreneurs. She always assumed she would start her own business; she'd worked with her father and stepmother in their insurance firm and knew the turf. Even when she worked for someone else, she was essentially self-employed.

“I recently blurted out on a podcast that I'm basically ungovernable,” she says.

Though steeped in traditional health insurance practices, she started to question “the way it's always been done” while representing a single voluntary benefits carrier. “That was more like being self-employed than entrepreneurial. I got a commission check from one carrier, had a marketing team, didn't invoice, didn't have to build a website. I didn't do any of that.”

The money was good, but something wasn't right. “I saw things happening that I thought I could fix and they weren't being fixed by anyone I knew. I was questioning things. I thought I could offer something valuable to an employer.”

Before she took the leap into her current business, she tested the startup waters by launching an enrollment service. Although that venture took far more time and energy than she had anticipated, she knew she had to follow her passion all the way into consulting.

Megan Cook's career track represents a blend of De Paoli and Berkowitz. Like De Paoli, she comes from an entrepreneurial family. Like Berkowitz, she got into the broker business in 2006, just before the recession, and was not highly influenced by traditional health insurance marketing. “Owning my own business was always in the back of my mind,” she says. When her employer was purchased in 2015, she was ready to strike out on her own. She knew exactly what she wanted to do and had a target market. She was ready.

Learning to fly

Niko Caparisos never wavered from his resolve to run a startup insurance provider. He told his first boss that was his intention, and after just four years as an employee, he struck out on his own.

“Knowing that I wanted to serve my clients in new ways, starting my own agency was the only route to take,” he says. “I was ready to make decisions with my clients without interference, but still had the support of many willing to help me.” He founded Prosperity Benefits in 2012 with a specific plan in mind for Year One. As with most plans, his changed. But he wasn't daunted by the process.

“The first year, I spent a large amount of time retooling my approach, offerings, workflow, technology and other differentiators. It was exciting to be establishing a new company and brand while being committed to making positive changes for my current and future clients,” he says. “Much of my time was spent reading 5500s, looking up publicly available RFPs, websites, presentations, etc. I was obsessed with scaling down large employer solutions to a market that had never seen these innovations.”

That first year strains some to their limits. “I don't know if I'd have the stomach to do that again,” Berkowitz says, “but it forced me to operate at a level that I never suspected was in me.”

Kareim Cade is more specific about his own post-launch pain points. Although he had longed to hang out his own shingle and change the way benefits and health insurance worked, he had moments of extreme doubt that first year.

“I encountered just about every unexpected bump in the road that one can encounter in the early days,” he recalls. “The mortgage was behind, the cars were in jeopardy of being repossessed, I ate at Fridays damn near daily because I had reward points, the unfriendly 1-800 numbers were on the answering machine threatening collection, I had to make payroll for my assistant, my then-spouse was very uncomfortable, my confidence was shaken, and my self-esteem was rattled. I heard 'no' daily.”

Cade says that, upon reflection, he may have pushed a bit too hard that first year.

“If I had to do it over, I would be sure to maintain balance earlier in my career. At the time, everything is about growing the business, because it all depends upon you. I was obsessed with proving to myself that I could make it happen and live out my dreams. The model caused me to leave some carnage behind in areas of my personal life.”

But he did, in fact, go on to succeed, as have others. Perseverance is clearly a common characteristic. Cook remembers when she finally realized that her business plan to sell wellness and nutrition programs to employers was not going to work. She had to find another focus. But she was not going back to a staff job.

“I did wellness and nutrition for a year and could see it was not going to move the needle,” she says. It was a hard pill to swallow. “You don't know what you're in for, how difficult that first year is going to be, the skills it will require. But you learn on the fly.”

Importantly for Cook, she met Dave Chase, founder of Health Rosetta. Suddenly, everything got … well, if not easier, better. Rather than learning on the fly, she began to soar.

Airborne, with co-pilots

Berkowitz says he met prospective clients morning, noon and night his first year. After 12 months, he had a client list with 28 names on it. “I still don't know how it happened; it was a blur,” he says.

As he entered Year Two, his confidence restored, he focused on a more basic challenge: educating his potential clients about the innovative benefits he offered.

“It's all about educating our market. I go where there are CEOs, COOs, CFOs, HR directors. Those in the driver's seat who can make a decision. Unless people know you and what you are offering, you can't change anything. That's where the rubber meets the road.”

Like Cook, he connected with Health Rosetta. They were among the first 30 advisors to be certified. Both agree that the community of broker-consultants gathered around Health Rosetta has been a major driver of their success.

De Paoli looked elsewhere for her network. The members of her Mastermind group have provided a solid support network. “There are 40 of us, and between the 40, we have seen and done it all.”

She also found her marketing sweet spot. She gave networking events a go but “although I met some lovely people, they were all doing the same thing: selling.”

Her solution? Live events. Webinars and presentations got her in front of the right people and moved the needle.

“I have learned an incredible amount about marketing and sales,” she says. “All sales is leadership. I have to help that person make a good decision for themselves. If it does not involve working with me, that's OK.”

Caparisos stuck with his goals-oriented strategy and is now ready to take on larger clients.

“As with many small business owners, I had benchmarks to achieve,” he says. “Typically, I was aiming for revenue goals as I began. After surpassing each subsequent mark, I realized that it would be more expeditious to shift my attention to working with larger employers to solve some of their complex problems. Helping more people means serving larger employers. The need in the market is evident, to say the least.”

Cade has seen his business grow rapidly since that first year. He gives a large amount of credit to the advice he received from mentors.

“As I always say, 'Mentorship is the shortcut to success.' The first person that I turned to for advice was my mother,” also a successful insurance agent. “She then began to connect me to other successful entrepreneurs who provided additional perspective on what it took to survive in the early years while building the business. It wasn't until later in my career that I could afford professional consultants who could come in and shed additional wisdom and insight. I was able to combine my early years of wisdom from my mentors with my professional consultants' advice and the rest, as they say, is history.”

A history that's still being written.

Meanwhile, Cook can now look back with satisfaction on her first-year perseverance. She says the transition from Year One to Year Two was eased by her husband's “regular” job, with set hours, a weekly paycheck and health insurance. “It would have been really hard had I been the breadwinner then,” she says, adding that the couple also had their first child that year.

Now, her gamble to start her own company is paying off—and not just financially.

“This morning, I took my little guy out on a walk in the sunshine, and didn't start work till 9. I have better work-life balance than ever before. I work from home 50 percent of the time and I can even get in a workout during the day.”

Her next challenge: Scaling the business to take on larger clients. While she first targeted small to mid-sized employers, she believes, as does Caparisos, that she can influence more lives by working with employers with 1,000 or more lives covered. With help from her friends at Health Rosetta and Seattle's Vistage group, she believes she will figure out that challenge, as well.

Eight miles high

Certainly, being your own boss is not for everyone. As our entrepreneurs report, there's a price to be paid for going out on your own—especially if your mission is to break new ground in a tradition-bound industry. The failure rate for startups is shockingly high; the Small Business Administration says 30 percent go under after a year and only half of them make it past Year Five. The toll on one's personal life varies, but that too is significant. Money is a constant worry.

But for those like De Paoli, who are “ungovernable,” doing it “my way” is, in the long run, the only way. These five consultants represent just a small fraction of those out there who are focused on innovative products and redefining the industry. Freed of bureaucracies, of having to ask permission, they can move the needle more quickly on benefits and health care. When drive and mission ascend together, you better cover your ears. A sonic boom is coming.

Flying lessons

We asked our five advisors whether they would recommend entrepreneurship to a friend or esteemed colleague. What qualities forecast success as an entrepreneur? Here's what they told us:

Megan Cook: “I would, depending on the person. Do a thorough self-assessment. First, you need to have sales experience. Then a really incredible work ethic. Third, resilience. Ask yourself, can you get kicked in the face a few hundred times and still keep going?”

Niko Caparisos: “I certainly would, and have, for years. The rewards of owning your agency are evident even in the early years as you scrap to grow your enterprise. At several junctures, I have considered employment options with larger firms but have each time decided to buckle down in my own efforts. Hindsight is always 20-20, but working harder and smarter helps your chances.”

Kareim Cade: “I would definitely recommend starting your own business. If you have passion, work ethic, integrity, the right motives and thick skin, you can start and grow a successful business. This country continues to thrive on the innovative and creative small-business owner who has found a solution to a problem and filled it. The key is to go in with your eyes wide open, knowing that it will not be easy, but it will be satisfying to know that you took a product or concept from ideation to creation to implementation.”

Allison De Paoli: “Do a self-assessment. Ask yourself, are you comfortable making decisions? Can you make them quickly? Are you comfortable with good and not perfect? Are you flexible? Are you comfortable with insecurity? If yes to those, go for it!”

Adam Berkowitz: “Oh hell yes, I would recommend it! Buckle up. It's a thrill ride. Make sure you get your family on board. It won't work without that.”

A family affair

By Maggie Taylor Berkowitz

Maggie Taylor Berkowitz is the spouse of Adam Berkowitz. We asked her to describe the entrepreneurial process from her viewpoint. Here's what she had to say.

On July 30, 2016 our lives changed forever. My son, James, entered the world and made himself known immediately. And my husband, Adam, was forced to exit the only job he'd known since college, where he had risen to the top of the organization.

It took only minutes after learning that his email had been locked out for us to decide that no person, no event, and certainly no former employer was going to rob us of the joy of welcoming our first child. We circled the wagons and went about the business of rebuilding as a family of three. While I recovered from a physically traumatic delivery and subsequent surgery, and later battled with postpartum depression, Adam was there each step of the way, holding our family up and making big plans for the future.

Having a child puts everything in perspective, and we came to the decision that whatever Adam's next move was, it had to be something he was passionate about, something worthy of walking out the door each morning as he kissed us goodbye. For my husband, that thing was redesigning the benefits experience in a way that saved employers money, streamlined processes, and allowed employees to actually get excited about benefits. We often joked that we really had two babies that year: James and Simpara. Adam's passion and love for this industry is really incredible. His drive to bring the absolute best experience to people, to further connect and serve his clients in a way that feels authentic, pushes the boundaries of what even I knew was possible.

Almost three years later, I am incredibly thankful for the words we first wrote on a business plan as sleep-deprived new parents: Simpara is about people: The restaurant server who was able to get health coverage for her husband's cancer treatments; the mid level employee who writes an email saying, “who knew benefits could actually be this exciting?!”; and the business owners offering better options at lower costs to hundreds of employees. These are the people that make that goodbye every morning worth it. And thankfully when our second son, Quinn, was born December 12, 2018, the hospital had strong Wi-Fi, because Adam's email was certainly up and running that day.